Monoamine compound and organic electroluminescence device including the same

ABSTRACT

Provided are a monoamine compound and an organic electroluminescence device including the same. The monoamine compound according to an example embodiment is represented by the following Formula 1

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation of U.S. patent application Ser. No.15/789,274, filed on Oct. 20, 2017, which claims priority to KoreanPatent Application Nos. 10-2016-0137914, filed on Oct. 21, 2016,10-2017-0065359, filed on May 26, 2017, and 10-2017-0114951, filed onSep. 8, 2017, and entitled: “Monoamine Compound and OrganicElectroluminescence Device Including the Same,” are each incorporated byreference herein in its entirety.

BACKGROUND 1. Field

Embodiments relate to a compound and an organic electroluminescencedevice including the same.

2. Description of the Related Art

An organic electroluminescence display is a so called self-luminescentdisplay. In the organic electroluminescence display, recombination ofholes and electrons injected from a first electrode and a secondelectrode in an emission layer may create emitted light. A luminescentmaterial, for example, an organic compound, may be in the emissionlayer.

SUMMARY

Embodiments are directed to a monoamine compound represented by thefollowing Formula 1:

In Formula 1, L₁ may be a substituted or unsubstituted arylene grouphaving 6 to 30 carbon atoms for forming a ring, or a substituted orunsubstituted heteroarylene group having 2 to 30 carbon atoms forforming a ring, n may be 1 or 2, L₂ and L₃ may each independently be adirect linkage, a substituted or unsubstituted arylene group having 6 to30 carbon atoms for forming a ring, or a substituted or unsubstitutedheteroarylene group having 2 to 30 carbon atoms for forming a ring, R₁may be a substituted or unsubstituted alkyl group having 1 to 10 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30 carbonatoms for forming a ring, a substituted or unsubstituted heteroarylgroup having 2 to 30 carbon atoms for forming a ring, or a substitutedor unsubstituted aryl silyl group, and Ar₁ and Ar₂ may eachindependently be a substituted or unsubstituted aryl group having 6 to30 carbon atoms for forming a ring, or a substituted or unsubstitutedheteroaryl group having 2 to 30 carbon atoms for forming a ring.

In an embodiment, the monoamine compound represented by Formula 1 may berepresented by the following Formula 2-1 or 2-2:

In Formulae 2-1 and 2-2, m₁ may be 0 or 1, m₂ may be an integer of 0 to2, R₂ may be a hydrogen atom, a deuterium atom, a substituted orunsubstituted alkyl group having 1 to 10 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,a substituted or unsubstituted heteroaryl group having 2 to 30 carbonatoms for forming a ring, or a substituted or unsubstituted aryl silylgroup, or may be combined with an adjacent group to form a ring, andAr₁, Ar₂, L₁, L₂, L₃, and R₁ are the same as described above.

In an embodiment, the monoamine compound represented by Formula 2-1 maybe represented by one of the following Formulae 2-1-1 to 2-1-3:

In Formulae 2-1-1 to 2-1-3, Ar₁ and Ar₂, L₂ and L₃, and R₁ are the sameas described above.

In an embodiment, the monoamine compound represented by Formula 2-2 maybe represented by one of the following Formulae 2-2-1 to 2-2-3.

In Formulae 2-2-1 to 2-2-3, Ar₁ and Ar₂, L₂ and L₃ and R₁ are the sameas described above.

R₁ may be a substituted or unsubstituted phenyl group, L₃ may be asubstituted or unsubstituted phenylene group, and Ar₂ may be asubstituted or unsubstituted naphthyl group.

L₂ may be a substituted or unsubstituted phenylene group, and Ar₁ may bea substituted or unsubstituted phenyl group.

L₂ may be a direct linkage, and Ar₁ may be a substituted orunsubstituted dibenzofuranyl group.

In an embodiment, L₁ may be a substituted or unsubstituted phenylenegroup, a substituted or unsubstituted divalent biphenyl group, or asubstituted or unsubstituted naphthylene group.

In an embodiment, R₁ may be a substituted or unsubstituted phenyl group,a substituted or unsubstituted naphthyl group, a substituted orunsubstituted biphenyl group, or a substituted or unsubstitutednitrogen-containing heteroaryl group.

In an embodiment, Ar₁ and Ar₂ may each independently be a substituted orunsubstituted phenyl group, a substituted or unsubstituted biphenylgroup, a substituted or unsubstituted terphenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted phenanthrylgroup, or a substituted or unsubstituted fluorenyl group.

In an embodiment, Ar₁ and Ar₂ may each independently be a substituted orunsubstituted dibenzofuranyl group, a substituted or unsubstituteddibenzothiophenyl group, a substituted or unsubstitutedbenzonaphthofuranyl group, or a substituted or unsubstitutedbenzonaphthothiophenyl group.

In an embodiment, Ar₁ and Ar₂ may each independently be represented bythe following Formula 3:

in case Ar₁ and Ar₂ are each independently represented by Formula 3, informula 1, L₂ and L₃ may each independently be a substituted orunsubstituted arylene group having 6 to 30 carbon atoms for forming aring, or a substituted or unsubstituted heteroarylene group having 2 to30 carbon atoms for forming a ring In formula 3, R₃ is a substituted orunsubstituted alkyl group having 1 to 10 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,a substituted or unsubstituted heteroaryl group having 2 to 30 carbonatoms for forming a ring, or a substituted or unsubstituted aryl silylgroup.

In an embodiment, Ar₁ and Ar₂ may each independently be represented bythe following Formula 4:

In Formula 4, X is O or S, R₄ and R₅ may each independently be ahydrogen atom, a deuterium atom, a substituted or unsubstituted alkylgroup having 1 to 10 carbon atoms, a substituted or unsubstituted arylgroup having 6 to 30 carbon atoms for forming a ring, a substituted orunsubstituted heteroaryl group having 2 to 30 carbon atoms for forming aring, or a substituted or unsubstituted aryl silyl group, p may be aninteger of 0 to 4, and q may be an interger of 0 to 3.

In an embodiment, L₂ and L₃ may each independently be a direct linkage,a substituted or unsubstituted phenylene group, a substituted orunsubstituted divalent biphenyl group, or a substituted or unsubstitutednaphthylene group.

In an example embodiment, an organic electroluminescence device includesa first electrode, a hole transport region provided on the firstelectrode, an emission layer provided on the hole transport region, anelectron transport region provided on the emission layer, and a secondelectrode provided on the electron transport region. At least one of thehole transport region, the emission region, and the electron transportregion includes a monoamine compound represented by the followingFormula 1:

In Formula 1, L₁ may be a substituted or unsubstituted arylene grouphaving 6 to 30 carbon atoms for forming a ring, or a substituted orunsubstituted heteroarylene group having 2 to 30 carbon atoms forforming a ring, n may be 1 or 2, L₂ and L₃ may each independently be adirect linkage, a substituted or unsubstituted arylene group having 6 to30 carbon atoms for forming a ring, or a substituted or unsubstitutedheteroarylene group having 2 to 30 carbon atoms for forming a ring, R₁may be a substituted or unsubstituted alkyl group having 1 to 10 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30 carbonatoms for forming a ring, a substituted or unsubstituted heteroarylgroup having 2 to 30 carbon atoms for forming a ring, or a substitutedor unsubstituted aryl silyl group, and Ar₁ and Ar₂ may eachindependently be a substituted or unsubstituted aryl group having 6 to30 carbon atoms for forming a ring, or a substituted or unsubstitutedheteroaryl group having 2 to 30 carbon atoms for forming a ring.

In an embodiment, the hole transport region may include the monoaminecompound represented by Formula 1.

In an embodiment, the hole transport region may include a hole injectionlayer disposed on the first electrode and a hole transport layerdisposed on the hole injection layer, and the hole transport layer mayinclude the monoamine compound represented by Formula 1.

In an embodiment, the hole transport layer may make contact with theemission layer.

In an embodiment, the hole transport region may include a hole injectionlayer disposed on the first electrode, a first hole transport layerdisposed on the hole injection layer, and a second hole transport layerdisposed on the first hole transport layer and adjacent to the emissionlayer, wherein the second hole transport layer includes the monoaminecompound represented by Formula 1.

BRIEF DESCRIPTION OF THE FIGURES

Features will become apparent to those of skill in the art by describingin detail example embodiments with reference to the attached drawings inwhich:

FIG. 1 illustrates a schematic cross-sectional view of an organicelectroluminescence device according to an example embodiment;

FIG. 2 illustrates a schematic cross-sectional view of an organicelectroluminescence device according to an example embodiment; and

FIG. 3 illustrates a schematic cross-sectional view of an organicelectroluminescence device according to an example embodiment.

DETAILED DESCRIPTION

Example embodiments will now be described more fully hereinafter withreference to the accompanying drawings; however, they may be embodied indifferent forms and should not be construed as limited to theembodiments set forth herein. Rather, these embodiments are provided sothat this disclosure will be thorough and complete, and will fullyconvey example implementations to those skilled in the art. In thedrawing figures, the dimensions of layers and regions may be exaggeratedfor clarity of illustration. Like reference numerals refer to likeelements throughout.

It will be understood that, although the terms first, second, etc. maybe used herein to describe various elements, these elements should notbe limited by these terms. These terms are only used to distinguish oneelement from another element. For example, a first element discussedbelow could be termed a second element, and similarly, a second elementcould be termed a first element. As used herein, the singular forms areintended to include the plural forms as well, unless the context clearlyindicates otherwise.

It will be further understood that the terms “comprises” or“comprising,” when used in this specification, specify the presence ofstated features, numerals, steps, operations, elements, parts, or acombination thereof, but do not preclude the presence or addition of oneor more other features, numerals, steps, operations, elements, parts, ora combination thereof. It will also be understood that when a layer, afilm, a region, a plate, etc. is referred to as being ‘on’ another part,it can be directly on the other part, or intervening layers may also bepresent. On the contrary, when a layer, a film, a region, a plate, etc.is referred to as being ‘under’ another part, it can be directly underthe other part, or intervening layers may also be present.

In the present disclosure,

means a part to be connected.

In the present disclosure, “substituted or unsubstituted” may meansubstituted with at least one substituent selected from the groupconsisting of deuterium, halogen, cyano, nitro, silyl, boron, arylamine, phosphine oxide, phosphine sulfide, alkyl, alkenyl, aryl, andheterocycle or unsubstituted. In addition, each of the substituentillustrated above may be substituted or unsubstituted. For example,biphenyl may be interpreted as aryl, or phenyl substituted with phenyl.

In the present disclosure, the terms “forming a ring by combiningadjacent groups with each other” may mean forming a substituted orunsubstituted hydrocarbon ring or a substituted or unsubstitutedheterocycle by combining adjacent groups with each other. A hydrocarbonring may include an aliphatic hydrocarbon ring and an aromatichydrocarbon ring. The heterocycle may include an aliphatic heterocycleand aromatic heterocycle. The hydrocarbon ring and heterocycle may be amonocycle or polycycle. In addition, the ring formed by combiningadjacent groups may be connected with another ring to form a spirostructure.

In the present disclosure, the terms “an adjacent group” may mean asubstituent at an atom which is directly connected with another atom atwhich a corresponding substituent is substituted, another substituent atan atom at which a corresponding substituent is substituted, or asubstituent stereoscopically disposed at the nearest position to acorresponding substituent. For example, two methyl groups in1,2-dimethylbenzene may be interpreted as “adjacent groups”, and twoethyl groups in 1,1-diethylcyclopentene may be interpreted as “adjacentgroups”.

In the present disclosure, a direct linkage may mean a single bond.

In the present disclosure, a halogen atom may include a fluorine atom, achlorine atom, a bromine atom, or an iodine atom.

In the present disclosure, the alkyl may have a linear, branched, orcyclic shape. The carbon number of the alkyl may be 1 to 30, 1 to 20, 1to 15, 1 to 10, or 1 to 6. Examples of the alkyl may include methyl,ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, i-butyl,2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl,t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl,4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl,cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl,1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl,n-octyl, t-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl,3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl,2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl,n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl,2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl,2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl,n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyl eicosyl,2-butyl eicosyl, 2-hexyl eicosyl, 2-octyl eicosyl, n-heneicosyl,n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl,n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc., withoutlimitation.

In the present disclosure, the aryl means an optional functional groupor substituent derived from an aromatic hydrocarbon ring. The aryl maybe monocyclic aryl or polycyclic aryl. The carbon number of the aryl forforming a ring may be 6 to 30, 6 to 20, or 6 to 15. Examples of the arylmay include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl,biphenyl, terphenyl, quaterphenyl, quinquephenyl, sexiphenyl,triphenylenyl, pyrenyl, benzofluoranthenyl, chrysenyl, etc., withoutlimitation.

In the present disclosure, the fluorenyl may be substituted, or twosubstituents may be combined with each other to form a spiro structure.For example, the fluorenyl may be 9,9′-spirobifluorenyl.

In the present disclosure, the heteroaryl may be heteroaryl including atleast one of O, N, P, S, or Si as a heteroatom. The heteroaryl may bemonocyclic heteroaryl or polycyclic heteroaryl. The carbon number of theheteroaryl for forming a ring may be 2 to 30, or 2 to 20. Examples ofthe heteroaryl may include thiophenyl, furanyl, pyrrolyl, imidazolyl,thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl,pyrimidyl, triazinyl, acridyl, pyridazinyl, pyrazinyl, quinolinyl,quinazolinyl, quinoxalinyl, phenoxazyl, phthalazinyl, pyridopyrimidinyl, pyrido pyrazinyl, pyrazino pyrazinyl, isoquinolinyl,indolyl, carbazolyl, N-arylcarbazolyl, N-heteroaryl carbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl,benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiophenyl,benzofuranyl, phenanthroline, isooxazolyl, thiadiazolyl, phenothiazinyl,dibenzosilolyl, dibenzofuranyl, etc., without limitation.

In the present disclosure, the explanation on the aryl may be applied tothe arylene, except that the arylene is divalent. The explanation on theheteroaryl may be applied to the heteroarylene, except that theheteroarylene is divalent.

In the present disclosure, the silyl may include alkyl silyl and arylsilyl. Examples of the silyl may include trimethylsilyl, triethylsilyl,t-butyl dimethylsilyl, vinyl dimethylsilyl, propyl dimethylsilyl,triphenylsilyl, diphenylsilyl, phenylsilyl, etc., without limitation.

In the present disclosure, the boron may include alkyl boron and arylboron. Examples of the boron may include trimethyl boron, triethylboron, t-butyl dimethyl boron, triphenyl boron, diphenyl boron, phenylboron, etc., without limitation.

In the present disclosure, the alkenyl may be linear or branched. Thecarbon number is not specifically limited, however may be 2 to 30, 2 to20, or 2 to 10. Examples of the alkenyl may include vinyl, 1-butenyl,1-pentenyl, 1,3-butadienyl, styrenyl, styrylvinyl, etc., withoutlimitation.

In the present disclosure, the carbon number of the amine is notspecifically limited, however may be 1 to 30. The amine may includealkyl amine and aryl amine. Examples of the amine may includemethylamine, dimethylamine, phenylamine, diphenylamine, naphthylamine,9-methyl-anthracenylamine, triphenylamine, etc., without limitation.

Hereinafter, a monoamine compound according to an example embodimentwill be explained.

In an example embodiment, the monoamine compound may be represented bythe following Formula 1:

In Formula 1, L₁ may be a substituted or unsubstituted arylene grouphaving 6 to 30 carbon atoms for forming a ring, or a substituted orunsubstituted heteroarylene group having 2 to 30 carbon atoms forforming a ring. L₁ may be a substituted or unsubstituted phenylenegroup. L₁ may be a substituted or unsubstituted divalent biphenyl group.L₁ may be a substituted or unsubstituted naphthylene group.

L₁ may be a substituted or unsubstituted arylene group having 6 to 15carbon atoms for forming a ring.

L₁ may be an unsubstituted phenylene group. L₁ may be an m-phenylenegroup or a p-phenylene group. L₁ may be a monosubstituted phenylenegroup. For example, L₁ may be a phenylene group substituted with aphenyl group or a triphenylsilyl group.

L₁ may be an unsubstituted divalent biphenyl group. L₁ may be anunsubstituted naphthylene group.

Here, n is 1 or 2. In the case where n is 2, a plurality of L₁ may bethe same or different.

L₂ and L₃ may be the same or different. L₂ and L₃ are each independentlya direct linkage, a substituted or unsubstituted arylene group having 6to 30 carbon atoms for forming a ring, or a substituted or unsubstitutedheteroarylene group having 2 to 30 carbon atoms for forming a ring. L₂and L₃ may each independently be a direct linkage, a substituted orunsubstituted phenylene group, or a substituted or unsubstituteddivalent biphenyl group. L₂ and L₃ may each independently be asubstituted or unsubstituted naphthylene group.

L₂ and L₃ may each independently be an unsubstituted divalent phenylenegroup. L₂ and L₃ may each independently be an m-phenylene group or ap-phenylene group. Each of L₂ and L₃ may be a monosubstituted phenylenegroup. Each of L₂ and L₃ may be a phenylene group substituted with analkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30carbon atoms. For example, each of L₂ and L₃ may be a phenylene groupsubstituted with a methyl group or a phenyl group.

L₂ and L₃ may each independently be an unsubstituted divalent biphenylgroup. L₂ and L₃ may each independently be an unsubstituted naphthylenegroup.

R₁ is an alkyl group having 1 to 10 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,a substituted or unsubstituted heteroaryl group having 2 to 30 carbonatoms for forming a ring, or a substituted or unsubstituted aryl silylgroup. R₁ may be a substituted or unsubstituted phenyl group, asubstituted or unsubstituted naphthyl group, a substituted orunsubstituted biphenyl group, or a substituted or unsubstitutednitrogen-containing heteroaryl group. For example, R₁ may be a pyridinylgroup or a triphenylsilyl group.

R₁ may be a monosubstituted phenyl group. R₁ may be a deuterium atom, ahalogen atom, a cyano group, or a phenyl group substituted with an alkylgroup having 1 to 10 carbon atoms. For example, R₁ may be a phenyl groupsubstituted with a cyano group or an isopropyl group.

Ar₁ and Ar₂ may be the same or different. Ar₁ and Ar₂ are eachindependently a substituted or unsubstituted aryl group having 6 to 30carbon atoms for forming a ring, or a substituted or unsubstitutedheteroaryl group having 2 to 30 carbon atoms for forming a ring. Ar₁ andAr₂ will be described in detail below.

In an example embodiment, in Formula 1, only the R₁ position in theillustrated phenanthryl group is substituted, and other positions arenot substituted. In the case where a substituent is positioned at theother positions of the phenanthryl group, the energy levels of the HOMOand LUMO of the phenanthryl group may change due to the substituent, andhole transport properties may be deteriorated. In an example embodiment,in a monoamine compound in which only the R₁ position of the phenanthrylgroup is substituted, hole transport properties may be enhanced for useof the monoamine compound as a hole transport material.

In example embodiments, Formula 1 may be represented by the followingFormula 2-1 or 2-2:

Here, m₁ may be 0 or 1, and m₂ may be an integer of 0 to 2.

R₂ may be a hydrogen atom, a deuterium atom, a substituted orunsubstituted alkyl group having 1 to 10 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,a substituted or unsubstituted heteroaryl group having 2 to 30 carbonatoms for forming a ring, or a substituted or unsubstituted aryl silylgroup. For example, R₂ may be a hydrogen atom, an unsubstituted phenylgroup, or a triphenylsilyl group.

In the case where m₂ is 2, a plurality of R₂ may be the same ordifferent. R₂ may be combined with an adjacent group to form a ring. Forexample, R₂ may be combined with an adjacent group to form a substitutedor unsubstituted hydrocarbon ring, or a substituted or unsubstitutedheterocycle. R₂ may be combined with an adjacent group to form asubstituted or unsubstituted aromatic hydrocarbon ring.

In Formulae 2-1 and 2-2, the particular explanation on Ar₁, Ar₂, L₁, L₂,L₃, and R₁ is the same as the explanation referring to Formula 1 andwill not be repeated.

Formula 2-1 may be represented by one of the following Formulae 2-1-1 to2-1-3:

In Formulae 2-1-1 to 2-1-3, Ar₁, Ar₂, L₂, L₃, and R₁ are the same asdefined in Formula 1.

In Formulae 2-1-1 to 2-1-3, R₁ may be a substituted or unsubstitutedphenyl group, L₃ may be a substituted or unsubstituted phenylene group,and Ar₂ may be a substituted or unsubstituted naphthyl group. Morespecifically, the monoamine compound may be represented by the followingFormula 2-1-1, R₁ may be a substituted or unsubstituted phenyl group, L₃may be a substituted or unsubstituted phenylene group, and Ar₂ may be asubstituted or unsubstituted naphthyl group. In case Ar₂ is asubstituted or unsubstituted naphthyl group, L₃ may be connected at thecarbon of position 1 of the naphthyl group.

In Formulae 2-1-1 to 2-1-3, L₂ may be a substituted or unsubstitutedphenylene group, and Ar₁ may be a substituted or unsubstituted phenylgroup. More specifically, the monoamine compound may be represented bythe following Formula 2-1-1, R₁ may be a substituted or unsubstitutedphenyl group, L₃ may be a substituted or unsubstituted phenylene group,Ar₂ may be a substituted or unsubstituted naphthyl group, L₂ may be asubstituted or unsubstituted phenylene group, and Ar₁ may be asubstituted or unsubstituted phenyl group.

In Formulae 2-1-1 to 2-1-3, L₂ may be a direct linkage, and Ar₁ may be asubstituted or unsubstituted dibenzofuranyl group. More specifically,the monoamine compound may be represented by the following Formula2-1-1, R₁ may be a substituted or unsubstituted phenyl group, L₃ may bea substituted or unsubstituted phenylene group, Ar₂ may be a substitutedor unsubstituted naphthyl group, L₂ may be a direct linkage, and Ar₁ maybe a substituted or unsubstituted dibenzofuranyl group.

Formula 2-2 may be represented by one of the following Formulae 2-2-1 to2-2-3:

In Formulae 2-2-1 to 2-2-3, Ar₁, Ar₂, L₂, L₃, and R₁ are the same asdefined in Formula 1.

In Formula 1, Ar₁ and Ar₂ may be each independently a substituted orunsubstituted phenyl group. Ar₁ and Ar₂ may each independently be amono- or di-substituted phenyl group. Ar₁ and Ar₂ may each independentlybe a phenyl group substituted with a deuterium atom, a halogen atom, acyano group, or an alkyl group having 1 to 10 carbon atoms. For example,Ar₁ and Ar₂ may each independently be a phenyl group substituted with afluorine atom or a substituted or unsubstituted octyl group.

Ar₁ and Ar₂ may each independently be a substituted or unsubstitutedbiphenyl group. Ar₁ and Ar₂ may each independently be a substituted orunsubstituted terphenyl group. An and Ar₂ may each independently be asubstituted or unsubstituted naphthyl group. Ar₁ and Ar₂ may eachindependently be a substituted or unsubstituted phenanthryl group.

Ar₁ and Ar₂ may each independently be a substituted or unsubstitutedfluorenyl group. Ar₁ and Ar₂ may each independently be a disubstitutedfluorenyl group. For example, An and Ar₂ may each independently be afluorenyl group substituted with an aryl group.

Ar₁ and Ar₂ may each independently be a substituted or unsubstituteddibenzofuranyl group. Ar₁ and Ar₂ may each independently be amonosubstituted dibenzofuranyl group. Ar₁ and Ar₂ may each independentlybe a dibenzofuranyl group substituted with an alkyl group having 1 to 10carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms for forming a ring, or a substituted or unsubstitutedheteroaryl group having 2 to 30 carbon atoms for forming a ring. Forexample, Ar₁ and Ar₂ may each independently be a dibenzofuranyl groupsubstituted with a phenyl group or a cyclohexyl group.

Ar₁ and Ar₂ may each independently be a substituted or unsubstituteddibenzothiophenyl group. Ar₁ and Ar₂ may each independently be asubstituted or unsubstituted benzonaphthofuranyl group. Ar₁ and Ar₂ mayeach independently be a substituted or unsubstitutedbenzonaphthothiophenyl group.

Ar₁ and Ar₂ may each independently be represented by the followingFormula 3:

R₃ may be an alkyl group having 1 to 10 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,a substituted or unsubstituted heteroaryl group having 2 to 30 carbonatoms for forming a ring, or a substituted or unsubstituted aryl silylgroup, and

indicates bonding to an adjacent moiety.

In the case where Ar₁ and Ar₂ are each independently represented byFormula 3, in formula 1, L₂ and L₃ may each independently be asubstituted or unsubstituted arylene group having 6 to 30 carbon atomsfor forming a ring, or a substituted or unsubstituted heteroarylenegroup having 2 to 30 carbon atoms for forming a ring.

In the case where Ar₁ and Ar₂ are each independently represented byFormula 3, in formula 1, L₂ and L₃ may each independently be asubstituted or unsubstituted phenylene group or a substituted orunsubstituted divalent biphenyl group. L₂ and L₃ may each independentlybe an unsubstituted phenylene group.

Ar₁ and Ar₂ may be represented by the following Formula 4:

X may be O or S.

R₄ and R₅ may each independently be a hydrogen atom, a deuterium atom, asubstituted or unsubstituted alkyl group having 1 to 10 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms forforming a ring, a substituted or unsubstituted heteroaryl group having 2to 30 carbon atoms for forming a ring, or a substituted or unsubstitutedaryl silyl group. R₄ and R₅ may each independently be a cycloalkylgroup. For example, R₄ and R₅ may each independently be a cyclohexylgroup.

“p” may be an integer of 0 to 4. “q” may be and integer of 0 to 3. Inthe case where “p” is an integer of 2 or more, a plurality of R₄ may bethe same or different. In the case where “q” is an integer of 2 or more,a plurality of R₅ may be the same or different. In the case where “p”and “q” are each independently an integer of 2 or more, R₄ and R₅ mayeach independently be combined with an adjacent group to form a ring.For example, in the case where at least one of R₄ and R₅ forms anaromatic ring, Ar₁ and Ar₂ may be a heteroaryl group having four or fiverings.

The monoamine compound represented by Formula 1 may be at least oneselected from the monoamine compounds represented in the followingCompound Group 1. However, an example embodiment is not limited thereto.

The monoamine compound according to an example embodiment may have arelatively large volume. Accordingly, when the monoamine compoundrepresented by Formula 1 is applied to an organic electroluminescencedevice, high emission efficiency may be secured.

In particular, in an example embodiment, the monoamine compoundrepresented by Formula 1 has a phenanthryl group connected with an aminegroup via an arylene linker, and a substituent having a large volumesuch as an aryl group is positioned at an adjacent position to aposition where the phenanthryl group is connected with the arylenelinker.

Accordingly, steric repulsion may arise between the substituent and thearylene linker, the bonding angle between the phenanthryl group and thearylene linker may increase, and the volume occupied by the phenanthrylgroup may increase. Therefore, the monoamine compound according to anexample embodiment may decrease interaction between phenanthryl groups.The decrease of the interaction between the phenanthryl groups mayresult in the decrease of electron mobility. In the case where themonoamine compound according to an example embodiment is disposed in ahole transport layer HTL adjacent to an emission layer EML, thediffusion of electrons from the emission layer to a hole transportregion HTR may be restrained, and high emission efficiency of an organicelectroluminescence device may be secured.

Hereinafter, an organic electroluminescence device according to anexample embodiment will be explained. The explanation will be mainlygiven with difference features from the monoamine compound according toan example embodiment, and unexplained parts will follow theabove-description on the monoamine compound according to an exampleembodiment.

An organic electroluminescence device according to an example embodimentincludes the monoamine compound according to an example embodiment.

FIG. 1 is a schematic cross-sectional view illustrating an organicelectroluminescence device according to an example embodiment. FIG. 2 isa schematic cross-sectional view illustrating an organicelectroluminescence device according to an example embodiment. FIG. 3 isa schematic cross-sectional view illustrating an organicelectroluminescence device according to an example embodiment.

Referring to FIGS. 1 and 2, an organic electroluminescence device 10according to an example embodiment includes a first electrode EL1, ahole transport region HTR, an emission layer EML, an electron transportregion ETR, and a second electrode EL2.

The first electrode EL1 has electrical conductivity. The first electrodeEL1 may be, for example, a pixel electrode or an anode. The firstelectrode EL1 may be, for example, a transmissive electrode, atransflective electrode, or a reflective electrode. In the case wherethe first electrode EL1 is the transmissive electrode, the firstelectrode EL1 may be formed using, for example, a transparent metaloxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zincoxide (ZnO), or indium tin zinc oxide (ITZO). In the case where thefirst electrode EL1 is the transflective electrode or reflectiveelectrode, the first electrode EL1 may include, for example, Ag, Mg, Cu,Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, acompound thereof, or a mixture thereof (for example, a mixture of Ag andMg). Also, the first electrode EL1 may have a structure including aplurality of layers including a reflective layer or transflective layerformed using the above materials, and a transparent layer formed usingITO, IZO, ZnO, or ITZO.

The monoamine compound according to an example embodiment may beincluded in at least one organic layer provided between the firstelectrode EL1 and the second electrode EL2. Hereinafter, an embodimentthat includes the monoamine compound according to an example embodimentin a hole transport region HTR will be explained. However, embodimentsare not limited thereto, and, for example, the monoamine compoundaccording to an example embodiment may be included in an emission layerEML.

The organic electroluminescence device according to an exampleembodiment may include the monoamine compound represented by Formula 1in a hole transport region HTR. The hole transport region HTR mayinclude one or more monoamine compounds represented by Formula 1.

In Formula 1, the particular explanation on R₁, L₁ to L₃, n, Ar₁ and Ar₂is the same as the above description and will not be repeated.

Particular explanation on the monoamine compound represented by Formula1 may be applied as the above description and will not be repeated.

The hole transport region HTR may be provided on the first electrodeEL1. The hole transport region HTR may include at least one of a holeinjection layer HIL, a hole transport layer HTL, a hole buffer layer, oran electron blocking layer. The thickness of the hole transport regionHTR may be, for example, from about 1,000 Å to about 1,500 Å.

The hole transport region HTR may have, for example, a single layerformed using a single material, a single layer formed using a pluralityof different materials, or a multilayer structure including a pluralityof layers formed using a plurality of different materials.

For example, as shown in FIG. 2, the hole transport region HTR may havea single layer structure of a hole injection layer HIL or a holetransport layer HTL, or may have a single layer structure formed using ahole injection material and a hole transport material. In addition, thehole transport region HTR may have a single layer structure formed usinga plurality of different materials, or a laminated structure from thefirst electrode EL1 of hole injection layer HIL/hole transport layerHTL, hole injection layer HIL/hole transport layer HTL/hole bufferlayer, hole injection layer HIL/hole buffer layer, hole transport layerHTL/hole buffer layer, or hole injection layer HIL/hole transport layerHTL/electron blocking layer, without limitation.

As shown in FIG. 3, the hole transport region HTR may have a pluralityof hole transport layers. The hole transport region HTR may include afirst hole transport layer HTL1 and a second hole transport layer HTL2which is disposed on the first hole transport layer HTL1. The secondhole transport layer HTL2 may be a hole transport layer which isadjacent to the emission layer EML among the plurality of the holetransport layers.

The hole transport region HTR may be formed using various methods suchas a vacuum deposition method, a spin coating method, a cast method, aLangmuir-Blodgett (LB) method, an inkjet printing method, a laserprinting method, and a laser induced thermal imaging (LITI) method.

The hole transport region HTR may include the monoamine compoundaccording to an example embodiment as a hole transport material. Thelayer including the monoamine compound according to an exampleembodiment may be a hole transport layer HTL. In the case where the holetransport layer includes the first hole transport layer HTL1 and thesecond hole transport layer HTL2 as shown in FIG. 3, the monoaminecompound according to an example embodiment may be included in thesecond hole transport layer HTL2. The monoamine compound according to anexample embodiment may be included in an adjacent layer to the emissionlayer EML, in the hole transport region HTR.

In the case where the hole transport layer HTL includes the monoaminecompound according to an example embodiment, the hole injection layerHIL may include, for example, a phthalocyanine compound such as copperphthalocyanine; N,N′-diphenyl-N,N′-bis-[4-(phenyl-Mtolyl-amino)-phenyl]-biphenyl-4,4′-diamine (DNTPD),4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (M MTDATA),4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA),4,4′,4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/dodecylbenzenesulfonic acid (PANI/DB SA),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS),N,N′-di(naphthalene-1-yl)-N,N′-diphenyl-benzidine (NPB),triphenylamine-containing polyether ketone (TPAPEK),4-isopropyl-4′-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate,dipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile(HAT-CN), etc.

In the case where the hole transport layer HTL does not include themonoamine compound according to an embodiment, but, for example, theemission layer EML includes the monoamine compound according to anembodiment, the hole transport layer HTL may include, for example,carbazole derivatives such as N-phenyl carbazole, and polyvinylcarbazole, fluorine-based derivatives,N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), triphenylamine-based derivatives such as4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), 4,4′-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine] (TAPC),4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD),N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine,etc.

The thickness of the hole transport region HTR may be, for example, fromabout 100 Å to about 10,000 Å, for example, from about 100 Å to about1,000 Å. In the case where the hole transport region HTR includes boththe hole injection layer HIL and the hole transport layer HTL, thethickness of the hole injection layer HIL may be, for example, fromabout 100 Å to about 10,000 Å, for example, from about 100 Å to about1,000 Å, and the thickness of the hole transport layer HTL may be, forexample, from about 30 Å to about 1,000 Å. In the case where thethicknesses of the hole transport region HTR, the hole injection layerHIL, and the hole transport layer HTL satisfy the above-describedranges, satisfactory hole transport properties may be obtained withoutthe substantial increase of a driving voltage.

The hole transport region HTR may further include a charge generatingmaterial in addition to the above-described materials to improveconductivity. The charge generating material may be dispersed in thehole transport region HTR uniformly or non-uniformly. The chargegenerating material may be, for example, a p-dopant. The p-dopant may beone of quinone derivatives, metal oxides, or cyano group-containingcompounds, without limitation. For example, non-limiting examples of thep-dopant may include quinone derivatives such astetracyanoquinodimethane (TCNQ), and2,3,5,6-tetrafluoro-tetracyanoquinodimethane (F4-TCNQ), metal oxidessuch as tungsten oxide, and molybdenum oxide, without limitation.

As described above, the hole transport region HTR may further include atleast one of a hole buffer layer or an electron blocking layer inaddition to the hole injection layer HIL and the hole transport layerHTL. The hole buffer layer may compensate an optical resonance distanceaccording to the wavelength of light emitted from the emission layer EMLand increase light emission efficiency. Materials included in the holetransport region HTR may be used as materials included in the holebuffer layer. The electron blocking layer is a layer preventing electroninjection from the electron transport region ETR into the hole transportregion HTR.

The emission layer EML may be provided on the hole transport region HTR.

The thickness of the emission layer EML may be, for example, from about100 Å to about 300 Å. The emission layer EML may have a single layerformed using a single material, a single layer formed using a pluralityof different materials, or a multilayer structure having a plurality oflayers formed using a plurality of different materials.

The emission layer EML may emit, for example, one of red light, greenlight, blue light, white light, yellow light, or cyan light. Theemission layer EML may include, for example, a fluorescent material or aphosphorescent material. The emission layer EML may include a host and adopant. The emission layer EML may have a thickness of, for example,about 10 to about 60 nm.

The host material of the emission layer EML may be selected from, forexample, anthracene derivatives, fluoranthene derivatives, pyrenederivatives, arylacetylene derivatives, fluorene derivatives, perylenederivatives, chrysene derivatives, and phenanthrene derivatives, and mayfor example be pyrene derivatives, perylene derivatives, chrysenederivatives, phenanthrene derivatives, or anthracene derivatives. Forexample, anthracene derivatives represented by the following Formula 5may be used as the host material of the emission layer EML.

In Formula 5, Z₁ to Z₄ are each independently a hydrogen atom, adeuterium atom, a halogen atom, a substituted or unsubstituted silylgroup, a substituted or unsubstituted alkyl group having 1 to 15 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30 carbonatoms for forming a ring, or a substituted or unsubstituted heteroarylgroup having 2 to 30 carbon atoms for forming a ring, m₃ and m₄ are eachindependently an integer of 0 to 4, and m₅ and m₆ are each independentlyan integer of 0 to 5. In Formula 5, Z₃ and Z₄ may each independently becombined with an adjacent group to from a ring.

The compound represented by Formula 5 may be the compounds representedas the following structures. However, embodiments of the compoundrepresented by Formula 5 are not limited thereto.

The host may be or include, for example,tris(8-hydroxyquinolino)aluminum (Alq₃),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), poly(N-vinylcarbazole)(PVK), 9,10-di(naphthaline-2-yl)anthracene (ADN),4,4′,4″-tris(carbazol-9-yl)-triphenylamine (TCTA),1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBi),3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), distyrylarylene(DSA), 4,4′-bis(9-carbazolyl)-2,2′-dimethylbiphenyl (CDBP),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), etc.

The dopant may be or include, for example, styryl derivatives (forexample, 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB),4-(di-p-tolylamino)-4′-[(di-p-tolylamino)styryl]stilbene (DPAVB),N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine(N-BDAVBi)), perylene and the derivatives thereof (for example,2,5,8,11-tetra-t-butylperylene (TBP)), pyrene and the derivativesthereof (for example, 1,1-dipyrene, 1,4-dipyrenylbenzene,1,4-bis(N,N-diphenylamino)pyrene),N¹,N⁶-di(naphthalen-1-yl)-N¹,N⁶-diphenylpyrene-1,6-diamine, etc.

When the emission layer EML emits red light, the emission layer EML mayinclude, for example, tris(dibenzoylmethanato)phenanthroline europium(PBD:Eu(DBM)₃(Phen)), or a fluorescent material including perylene. Inthe case that the emission layer EML emits red light, the dopantincluded in the emission layer EML may be selected from, for example, ametal complex or an organometallic complex such asbis(1-phenylisoquinoline)acetylacetonate iridium (PIQIr(acac)),bis(1-phenylquinoline)acetylacetonate iridium (PQIr(acac),tris(1-phenylquinoline)iridium (PQIr), and octaethylporphyrin platinum(PtOEP), rubrene and the derivatives thereof, or4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) andthe derivatives thereof.

In the case where the emission layer EML emits green light, the emissionlayer EML may include, for example, a fluorescent material including,for example, tris(8-hydroxyquinolino)aluminum (Alq₃). In the case wherethe emission layer EML emits green light, the dopant included in theemission layer EML may be selected from, for example, a metal complex ororganometallic complex such as fac-tris(2-phenylpyridine)iridium(Ir(ppy)₃), or coumarin and the derivatives thereof.

In the case where the emission layer EML emits blue light, the emissionlayer EML may further include, for example, a fluorescent materialincluding, for example, one or more of spiro-DPVBi, spiro-6P,distyryl-benzene (DSB), distyryl-arylene (DSA), a polyfluorene(PFO)-based polymer, and a poly(p-phenylene vinylene) (PPV)-basedpolymer. In the case where the emission layer EML emits blue light, thedopant included in the emission layer EML may be selected from, forexample, a metal complex or an organometallic complexes such as(4,6-F₂ppy)₂Irpic, or perylene and the derivatives thereof.

The electron transport region ETR may be provided on the emission layerEML. The electron transport region ETR may include, for example, atleast one of an hole blocking layer, an electron transport layer ETL oran electron injection layer EIL, without limitation.

The electron transport region ETR may have, for example, a single layerformed using a single material, a single layer formed using a pluralityof different materials, or a multilayer structure having a plurality oflayers formed using a plurality of different materials.

For example, the electron transport region ETR may have a single layerstructure of the electron injection layer EIL or the electron transportlayer ETL, or a single layer structure formed using an electroninjection material and an electron transport material. In addition, theelectron transport region ETR may have a single layer structure having aplurality of different materials, or a structure laminated from thefirst electrode EL1 of electron transport layer ETL/electron injectionlayer EIL, or hole blocking layer/electron transport layer ETL/electroninjection layer EIL, without limitation. The thickness of the electrontransport region ETR may be, for example, from about 1,000 Å to about1,500 Å.

The electron transport region ETR may be formed using various methodssuch as a vacuum deposition method, a spin coating method, a castmethod, a Langmuir-Blodgett (LB) method, an inkjet printing method, alaser printing method, and a laser induced thermal imaging (LITI)method.

In the case where the electron transport region ETR includes theelectron transport layer ETL, the electron transport region ETR mayinclude, for example, tris(8-hydroxyquinolinato)aluminum (Alq₃),1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene,2,4,6-tris(3′-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine,2-(4-(N-phenylbenzoimidazolyl-1-ylphenyl)-9,10-dinaphthylanthracene,1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi),2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-diphenyl-1,10-phenanthroline (Bphen),3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ),4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ),2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD),bis(2-methyl-8-quinolinolato-N1,08)-(1,1′-biphenyl-4-olato)aluminum(BAlq), berylliumbis(benzoquinolin-10-olate (Bebq₂),9,10-di(naphthalene-2-yl)anthracene (ADN), or a mixture thereof, withoutlimitation. The thickness of the electron transport layer ETL may be,for example, from about 100 Å to about 1,000 Å and may be from about 150Å to about 500 Å. If the thickness of the electron transport layer ETLsatisfies the above-described range, satisfactory electron transportproperty may be obtained without substantial increase of a drivingvoltage.

When the electron transport region ETR includes the electron injectionlayer EIL, the electron injection layer EIL may include, for example, ametal such as Al, Ag, Li, Mg and Ca and a mixture thereof. However, anexample embodiment is not limited thereto. For example, the electroninjection layer EIL may use LiF, lithium quinolate (Liq), Li₂O, BaO,NaCl, CsF, a metal in lanthanides such as Yb, or a metal halide such asRbCl and RbI, without limitation. The electron injection layer EIL alsomay be formed using a mixture material of an electron transport materialand an insulating organo metal salt. The organo metal salt may be amaterial having an energy band gap of, for example, about 4 eV or more.For example, the organo metal salt may include a metal acetate, a metalbenzoate, a metal acetoacetate, a metal acetylacetonate, or a metalstearate. The thickness of the electron injection layer EIL may be, forexample, from about 1 Å to about 100 Å, and from about 3 Å to about 90Å. In the case where the thickness of the electron injection layer EILsatisfies the above described range, satisfactory electron injectionproperties may be obtained without inducing the substantial increase ofa driving voltage.

The electron transport region ETR may include a hole blocking layer, asdescribed above. The hole blocking layer may include at least one of,for example, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), or4,7-diphenyl-1,10-phenanthroline (Bphen), without limitation.

The second electrode EL2 may be provided on the electron transportregion ETR. The second electrode EL2 may be, for example, a commonelectrode or a cathode. The second electrode EL2 may be, for example, atransmissive electrode, a transflective electrode, or a reflectiveelectrode. In the case where the second electrode EL2 is thetransmissive electrode, the second electrode EL2 may be formed using,for example, ITO, IZO, ZnO, ITZO, etc.

In the case where the second electrode EL2 is the transflectiveelectrode or the reflective electrode, the second electrode EL2 mayinclude, for example, Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li,Ca, LiF/Ca, LiF/Al, Mo, Ti, a compound thereof, or a mixture thereof(for example, a mixture of Ag and Mg). The second electrode EL2 mayhave, for example, a multilayered structure including a reflective layeror a transflective layer formed using the above-described materials anda transparent conductive layer formed using ITO, IZO, ZnO, ITZO, etc.

In an implementation, the second electrode EL2 may be connected with anauxiliary electrode. In the case where the second electrode EL2 isconnected with the auxiliary electrode, the resistance of the secondelectrode EL2 may decrease.

In the organic electroluminescence device 10, according to theapplication of a voltage to each of the first electrode EL1 and secondelectrode EL2, holes injected from the first electrode EL1 may move viathe hole transport region HTR to the emission layer EML, and electronsinjected from the second electrode EL2 may move via the electrontransport region ETR to the emission layer EML. The electrons and theholes may recombine in the emission layer EML to generate excitons, andthe excitons may emit light via transition from an excited state to aground state.

In the case where the organic electroluminescence device 10 is a topemission type, the first electrode EL1 may be a reflective electrode,and the second electrode EL2 may be a transmissive electrode or atransflective electrode. In the case where the organicelectroluminescence device 10 is a bottom emission type, the firstelectrode EL1 may be a transmissive electrode or a transflectiveelectrode, and the second electrode EL2 may be a reflective electrode.

The organic electroluminescence device according to an exampleembodiment includes a monoamine compound represented by Formula 1, whichmay help provide high emission efficiency. The monoamine compoundrepresented by Formula 1 may have a relatively large volume. In anexample embodiment, in the monoamine compound represented by Formula 1,a phenanthryl group is connected with an amine group via an arylenelinker, and a substituent having a large volume such as an aryl group ispositioned at an adjacent position to a position where the phenanthrylgroup is connected with the arylene linker. Accordingly, stericrepulsion may arise between the substituent and the arylene linker, thebonding angle between the phenanthryl group and the arylene linker mayincrease, and the volume occupied by the phenanthryl group may increase.Therefore, a monoamine compound according to an example embodiment maydecrease interaction between phenanthryl groups. The decrease of theinteraction between the phenanthryl groups may result in the decrease ofelectron mobility. In the case where the monoamine compound according toan example embodiment is disposed in a hole transport layer HTL which isadjacent to an emission layer EML, the diffusion of electrons from theemission layer to a hole transport region HTR may be restrained, andhigh emission efficiency of an organic electroluminescence device may besecured.

The following Examples and Comparative Examples are provided in order tohighlight characteristics of one or more embodiments, but it will beunderstood that the Examples and Comparative Examples are not to beconstrued as limiting the scope of the embodiments, nor are theComparative Examples to be construed as being outside the scope of theembodiments. Further, it will be understood that the embodiments are notlimited to the particular details described in the Examples andComparative Examples.

Compounds according to example embodiments may be synthesized, forexample, as follows. However, an example embodiment is not limitedthereto.

SYNTHETIC EXAMPLES

1. Synthesis of Compound 1

Compound 1 which is a compound according to an example embodiment may besynthesized by the following reaction.

Under an argon (Ar) atmosphere, 4.30 g of Compound A, 9.98 g of CompoundB, 654 mg of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh₃)₄), and6.91 g of potassium carbonate (K₂CO₃) were added to a solvent of THF(200 ml)/water (50 ml) and deaerated. The reaction mixture was stirredand refluxed for 8 hours. After that, the reactant was cooled, extractedwith chloroform, and washed with a saturated saline solution. Theorganic layer thus obtained was dried with anhydrous sodium sulfate,filtered, and concentrated, and residues were separated by columnchromatography to obtain 5.29 g (yield 72%) of Compound 1 as a whitesolid. The molecular weight of the compound measured by FAB-MS was 649.In addition, the chemical shift values of the compound measured by¹H-NMR were 8.93 (m, 2H), 7.83 (m, 1H), 7.76-7.55 (12H), 7.51 (ddd, 1H,J=1, 7, 8 Hz), 7.47-7.34 (7H), 7.34-7.26 (2H), 7.26-7.19 (2H), 7.18-7.09(6H), 7.05 (ddd, 2H, J=2, 2, 9 Hz). From the results, the white solidcompound was identified as Compound 1.

Under an argon (Ar) atmosphere, 3.78 g of Compound A, 10.3 g of CompoundC, 575 mg of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh₃)₄), and6.34 g of potassium carbonate (K₂CO₃) were added to a solvent of THF(200 ml)/water (50 ml) and deaerated. The reaction mixture was stirredand refluxed for 8 hours. After that, the reactant was cooled, extractedwith chloroform, and washed with a saturated saline solution. Theorganic layer thus obtained was dried with anhydrous sodium sulfate,filtered, and concentrated, and residues were separated by columnchromatography to obtain 4.55 g (yield 63%) of Compound 12 as a whitesolid. The molecular weight of the compound measured by FAB-MS was 725.In addition, the chemical shift values of the compound measured by¹H-NMR were 8.93 (d, 2H, J=8 Hz), 7.74-7.55 (12H), 7.55-7.46 (6H),7.46-7.12 (19H). From the results, the white solid compound wasidentified as Compound 12.

Under an argon (Ar) atmosphere, 2.51 g of Compound A, 7.19 g of CompoundD, 381 mg of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh₃)₄), and5.31 g of potassium carbonate (K₂CO₃) were added to a solvent of THF(200 ml)/water (50 ml) and deaerated. The reaction mixture was stirredand refluxed for 8 hours. After that, the reactant was cooled, extractedwith chloroform, and washed with a saturated saline solution. Theorganic layer thus obtained was dried with anhydrous sodium sulfate,filtered, and concentrated, and residues were separated by columnchromatography to obtain 3.38 g (yield 68%) of Compound 38 as a whitesolid. The molecular weight of the compound measured by FAB-MS was 753.In addition, the chemical shift values of the compound measured by¹H-NMR were 8.87 (m, 2H), 7.96 (m, 2H), 7.92 (d, 2H, J=8H), 7.75 (m,1H), 7.71-7.50 (7H), 7.50-7.36 (5H), 7.36-7.10 (16H). From the results,the white solid compound was identified as Compound 38.

4. Synthesis of Compound 11

Under an argon (Ar) atmosphere, 10.0 g of Compound A, 29.2 g of CompoundE, 2.22 g of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh₃)₄), and431 mg of palladium acetate (Pd(OAc)₂) were added to a solvent oftoluene (300 ml)/ethyl alcohol (130 ml)/aqueous solution of 2 Mtripotassium orthophosphate (K₃PO₄) (64 ml), and deaerated. The reactionmixture was stirred and refluxed for 24 hours. After that, the reactionproduct was cooled, extracted with chloroform, and washed with asaturated saline solution.

The organic layer thus obtained was dried with anhydrous sodium sulfate,filtered, and concentrated, and residues were separated by columnchromatography to obtain 16.1 g (yield 69%) of Compound F as a whitesolid.

Under an argon (Ar) atmosphere, 4.01 g of Compound F, 3.89 g of CompoundG, 1.06 g of sodium t-butoxide, 316 mg ofbis(dibenzylideneacetone)palladium(0) (Pd(dba)₂), and 1.47 ml of 1.5 Mtoluene solution of tri-t-butyl phosphine (^(t)Bu₃P) were added to 150ml of toluene, and deaerated. The reaction mixture was stirred andrefluxed for 24 hours. After that, the reaction product was cooled,extracted with chloroform, and washed with a saturated saline solution.

The organic layer thus obtained was dried with anhydrous sodium sulfate,filtered, and concentrated, and residues were separated by columnchromatography to obtain 6.01 g (yield 84%) of Compound 11 as a whitesolid. The molecular weight of the compound measured by FAB-MS was 649.In addition, the chemical shift values of the compound measured by¹H-NMR were 8.88 (d, 2H, J=10 Hz), 7.76-7.43 (21H), 7.43-7.17 (5H), 7.09(ddd, 4H, J=2, 2, 8 Hz), 7.04-6.90 (3H). From the results, the whitesolid compound was identified as Compound 11.

5. Synthesis of Compound 16

Under an argon (Ar) atmosphere, 20.0 g of Compound A was stirred in 300ml of THF at −78° C. for 10 minutes, and 21.7 ml of n-butyllithium(n-BuLi) with 1.6 M concentration was slowly added thereto dropwiselyusing a dropping funnel, followed by additionally stirring for 30minutes. Then, 7.05 ml of trimethyl borate (B(OMe)₃) was slowly addedthereto dropwisely using a dropping funnel and additionally stirred atroom temperature for 3 hours. After that, 300 ml of 1 M HCl solution wasadded and extracted once. Then, the product thus obtained wasadditionally extracted three times using water and toluene. The organiclayer thus obtained was dried with anhydrous sodium sulfate, filtered,and concentrated, and residues were separated by column chromatographyto obtain 4.78 g (yield 30%) of Compound H as a white solid.

Under an argon (Ar) atmosphere, 4.50 g of Compound H, 4.04 g of CompoundI, 9.61 g of tripotassium orthophosphate (K₃PO₄), and 872 mg oftetrakis(triphenylphosphine)palladium(0) (Pd(PPh₃)₄), were added to asolvent of toluene (150 ml)/ethyl alcohol (10 ml)/water (5 ml), anddeaerated. The reaction mixture was stirred and refluxed for 24 hours.After that, the reaction product was cooled, extracted with chloroform,and washed with a saturated saline solution. The organic layer thusobtained was dried with anhydrous sodium sulfate, filtered, andconcentrated, and residues were separated by column chromatography toobtain 2.80 g (yield 42%) of Compound J as a white solid.

Under an argon (Ar) atmosphere, 2.45 g of Compound J, 1.79 g of CompoundG, 1.06 g of sodium t-butoxide, 152 mg oftris(dibenzylideneacetone)dipalladium(0) (Pd₂(dba)₃), and 0.21 ml of 1.6M toluene solution of tri-t-butyl phosphine (^(t)Bu₃P) were added to 150ml of xylene, and deaerated. The reaction mixture was stirred andrefluxed for 8 hours. After that, the reaction product was cooled,extracted with chloroform, and washed with a saturated saline solution.The organic layer thus obtained was dried with anhydrous sodium sulfate,filtered, and concentrated, and residues were separated by columnchromatography to obtain 3.11 g (yield 70%) of Compound 16 as a whitesolid. The molecular weight of the compound measured by FAB-MS was 725.In addition, the chemical shift values of the compound measured by¹H-NMR were 8.92 (d, 2H, J=8 Hz), 7.75-7.56 (11H), 7.56-6.95 (26H). Fromthe results, the white solid compound was identified as Compound 16.

Compound F was synthesized by the same synthetic method of Compound F inthe synthetic method of Compound 11. Then, under an argon (Ar)atmosphere, 5.00 g of Compound F, 5.21 g of Compound K, 1.32 g of sodiumt-butoxide, 390 mg of bis(dibenzylideneacetone)palladium(0) (Pd(dba)₂),and 1.83 ml of 1.5 M toluene solution of tri-t-butyl phosphine(^(t)Bu₃P) were added to 150 ml of toluene, and deaerated. The reactionmixture was stirred and refluxed for 24 hours. After that, the reactionproduct was cooled, extracted with chloroform, and washed with asaturated saline solution.

The organic layer thus obtained was dried with anhydrous sodium sulfate,filtered, and concentrated, and residues were separated by columnchromatography to obtain 6.65 g (yield 72%) of Compound 73 as a whitesolid. The molecular weight of the compound measured by FAB-MS was 673.In addition, the chemical shift values of the compound measured by¹H-NMR were 8.88 (d, 2H, J=9 Hz), 8.05-7.77 (6H), 7.72-7.60 (3H),7.60-7.27 (16H), 7.24 (m, 1H), 7.20-7.08 (3H), 6.97 (m, 2H), 6.92-6.82(2H). From the results, the white solid compound was identified asCompound 16.

Compound F was synthesized by the same synthetic method of Compound F inthe synthetic method of Compound 11. Then, under an argon (Ar)atmosphere, 4.20 g of Compound F, 4.70 g of Compound L, 1.11 g of sodiumt-butoxide, 331 mg of bis(dibenzylideneacetone)palladium(0) (Pd(dba)₂),and 1.53 ml of 1.5 M toluene solution of tri-t-butyl phosphine(^(t)Bu₃P) were added to 150 ml of toluene, and deaerated. The reactionmixture was stirred and refluxed for 24 hours. After that, the reactionproduct was cooled, extracted with chloroform, and washed with asaturated saline solution.

The organic layer thus obtained was dried with anhydrous sodium sulfate,filtered, and concentrated, and residues were separated by columnchromatography to obtain 6.93 g (yield 86%) of Compound 103 as a whitesolid. The molecular weight of the compound measured by FAB-MS was 699.In addition, the chemical shift values of the compound measured by¹H-NMR were 8.89 (d, 2H, J=8 Hz), 8.00 (d, 1H, J=8 Hz), 7.92 (dd, 1H,J=2, 8 Hz), 7.86 (d, 1H, J=8 Hz), 7.78-7.33 (21H), 7.33-7.20 (4H),7.20-7.03 (6H), 6.99 (ddd, 1H, J=1, 1, 8 Hz). From the results, thewhite solid compound was identified as Compound 103.

Compound F was synthesized by the same synthetic method of Compound F inthe synthetic method of Compound 11. Then, under an argon (Ar)atmosphere, 5.00 g of Compound F, 6.35 g of Compound M, 1.32 g of sodiumt-butoxide, 390 mg of bis(dibenzylideneacetone)palladium(0) (Pd(dba)₂),and 1.83 ml of 1.5 M toluene solution of tri-t-butyl phosphine(^(t)Bu₃P) were added to 150 ml of toluene, and deaerated. The reactionmixture was stirred and refluxed for 24 hours. After that, the reactionproduct was cooled, extracted with chloroform, and washed with asaturated saline solution.

The organic layer thus obtained was dried with anhydrous sodium sulfate,filtered, and concentrated, and residues were separated by columnchromatography to obtain 8.53 g (yield 83%) of Compound 104 as a whitesolid. The molecular weight of the compound measured by FAB-MS was 699.In addition, the chemical shift values of the compound measured by¹H-NMR were 8.90 (d, 2H, J=9 Hz), 8.02 (d, 2H, J=9 Hz), 7.92 (d, 2H, J=8Hz), 7.86 (d, 2H, J=8 Hz), 7.78-7.62 (3H), 7.62-7.40 (16H), 7.40-7.09(11H), 7.00 (m, 1H). From the results, the white solid compound wasidentified as Compound 104.

9. Synthesis of Compound 122

Under an argon (Ar) atmosphere, 7.25 g (28.3 mmol) of Compound N, 7.00 g(28.3 mmol) of Compound 0, 326 mg (0.566 mmol) ofbis(dibenzylideneacetone)palladium(0) (Pd(dba)₂), 0.687 ml (1.13 mmol)of a 1.65 M tri-t-butylphosphine (^(t)Bu₃P) solution, and 2.72 g (28.3mmol) of sodium t-butoxide were added to 200 ml of toluene, anddeaerated. The reaction mixture was stirred at about 90° C. for about 4hours. After that, the reaction product was cooled at room temperature,and treated with a filtration column, and the reaction product thusfiltered was concentrated. The concentrated reaction product wasrecrystallized with toluene-ethanol to obtain 7.30 g (18.9 mmol, yield67%) of Compound P.

Under an argon (Ar) atmosphere, 6.80 g (17.6 mmol) of Compound P, 6.44 g(17.6 mmol) of Compound F, 406 mg (0.706 mmol) ofbis(dibenzylideneacetone)palladium(0) (Pd(dba)₂), 0.856 ml (1.41 mmol)of a 1.65 M tri-t-butylphosphine (^(t)Bu₃P) solution, and 2.54 g (26.3mmol) of sodium t-butoxide were added to 200 ml of toluene, anddeaerated. The reaction mixture was heated and refluxed while heatingand stirring for about 20 hours. After that, the reaction product wascooled at room temperature, and treated with a filtration column, andthe reaction product thus filtered was concentrate. The concentratedreaction product was recrystallized with toluene-ethanol to obtain 8.52g (12.0 mmol, yield 68%) of Compound 122. The molecular weight of thecompound measured by FAB-MS was 713. In addition, the chemical shiftvalues of the compound measured by ¹H-NMR were 8.89 (d, 2H, J=9 Hz),8.05-7.82 (5H), 7.79-7.05 (27H), 6.99 (ddd, 1H, J=1.2 Hz, 1.2 Hz, 7.4Hz). From the results, the compound thus obtained was identified asCompound 122.

DEVICE MANUFACTURING EXAMPLES

Hereinafter, device manufacture and evaluation of emission efficiencyproperties were conducted twice with respect to devices having differentconfiguration.

Device Manufacturing Examples 1

Organic electroluminescence devices according to Examples 1 to 3 weremanufactured using Compounds 1, 12 and 38 as hole transport materials.

Example Compounds

Organic electroluminescence devices according to Comparative Examples 1to 6 were manufactured using Comparative Compounds c1 to c6 as holetransport materials.

Comparative Compounds

Organic electroluminescence devices according to Examples 1 to 3 andComparative Examples 1 to 6 were manufactured by forming a firstelectrode using ITO to a thickness of about 150 nm, a hole injectionlayer using tris naphthyl phenyl amino triphenylamine (TNATA) to athickness of about 60 nm, a hole transport layer using the compoundaccording to the example or the comparative example to a thickness ofabout 30 nm, an emission layer using dinaphthyl anthracene (ADN) dopedwith 3% tetra-t-butylperylene (TBP) to a thickness of about 25 nm, anelectron transport layer using tris(8-hydroxyquinolinato)aluminum (Alq₃)to a thickness of about 25 nm, an electron injection layer using LiF toa thickness of about 1 nm, and a second electrode using Al to athickness of about 100 nm. Each layer was formed by a vacuum depositionmethod.

Then, the emission efficiency of the organic electroluminescence devicethus manufactured was evaluated. The emission efficiency was measured asa relative emission efficiency ratio of each example and comparativeexample when considering the emission efficiency of an organicelectroluminescence device of Comparative Example 3 as 100%.

TABLE 1 Emission Efficiency Device (Relative Ratio Manufacturing HoleTransport Layer To Comparative Example Material Example 3) Example 1Example Compound 1 110%  Example 2 Example Compound 12 108%  Example 3Example Compound 38 106%  Comparative Comparative Compound c1 70%Example 1 Comparative Comparative Compound c2 98% Example 2 ComparativeComparative Compound c3 100%  Example 3 Comparative Comparative Compoundc4 92% Example 4 Comparative Comparative Compound c5 65% Example 5Comparative Comparative Compound c6 68% Example 6

Referring to the results of Table 1, emission efficiency was improvedfor Examples 1 to 3 when compared to that of Comparative Examples 1 to6. From the results in Table 1, it may be found that organicelectroluminescence devices including the compounds according to exampleembodiments may attain high emission efficiency.

In Examples 1 to 3, a monoamine compound including a phenyl group as anadjacent group to a position where a phenanthryl group and an arylenelinker are connected is included. Without being bound by theory, it isbelieved that a volume near a phenanthryl group in which a LUMO orbitalwhich is related to electron transportation is distributed, isincreased, while maintaining amine properties, and the transportation ofelectrons from an emission layer to a hole transport layer becomesdifficult, and thus, the concentration of excitons in the emission layeris increased to increase the emission efficiency.

In Comparative Example 3, a compound in which a phenanthryl group and anamine group are connected via an arylene linker is included, but thephenanthryl group in the compound included in Comparative Example 3 isnot substituted with a phenyl group. Accordingly, without being bound bytheory, it is believed that blocking effect of electrons transportedfrom an emission layer to a hole transport layer is not attained, andemission efficiency is lower than that of the examples.

In Comparative Example 4, a compound in which a phenyl group issubstituted at a phenanthryl group is included, but the phenyl group isnot substituted at a position adjacent to a position where thephenanthryl group and an arylene linker are connected, that is, not atthe carbon of position 10 of the phenanthryl group, but at the carbon ofposition 3. Accordingly, without being bound by theory, it is believedthat the volume increase at an active position, where a LUMO orbitalwhich is related to electron transportation is distributed, is notattained, and emission efficiency is reduced when compared to that ofthe examples.

In Comparative Examples 5 and 6, the devices included a diamine compoundhaving a low HOMO energy level, such that hole injection from a holeinjection layer to a hole transport layer may be deteriorated.Accordingly, emission efficiency was lower when compared to that of theexamples.

Device Manufacturing Examples 2

Organic electroluminescence devices according to Examples 4 to 12 weremanufactured using Compounds 1, 11, 12, 16, 38, 73, 103, 104, and 122 assecond hole transport materials.

Organic electroluminescence devices according to Comparative Examples 7to 15 were manufactured using Comparative Compounds c1 to c9 as holetransport materials.

Comparative Compounds

Organic electroluminescence devices according to Examples 4 to 11 and

Comparative Examples 7 to 15 were manufactured by forming a firstelectrode using ITO to a thickness of about 150 nm, a hole injectionlayer usingdipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile(HAT-CN) to a thickness of about 10 nm, a first hole transport layerusingN-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amineto a thickness of about 70 nm, a second hole transport layer using theexample compounds or comparative compounds to a thickness of about 10nm, an emission layer using(9-(4-(naphthalene-1-yl)phenyl)-10-perdeuterophenyl)anthracene dopedwith 3% N¹,N⁶-di(naphthalene-1-yl)-N¹,N⁶-diphenylpyrene-1,6-diamine to athickness of about 25 nm, an electron transport layer usingtris(8-hydroxyquinolinato)aluminum (Alq₃) to a thickness of about 25 nm,an electron injection layer using LiF to a thickness of about 1 nm, anda second electrode using Al to a thickness of about 100 nm. Each layerand the second electrode were formed by a vacuum deposition method.

Then, the emission efficiency of the organic electroluminescence devicethus manufactured was evaluated. The emission efficiency was measured asa relative emission efficiency ratio of each example and comparativeexample when considering the emission efficiency of an organicelectroluminescence device of Comparative Example 9 as 100%.

TABLE 2 Emission Efficiency Device (Relative Ratio Manufacturing SecondHole Transport To Comparative Example Layer Example 9) Example 4 ExampleCompound 1 110% Example 5 Example Compound 11 110% Example 6 ExampleCompound 12 110% Example 7 Example Compound 16 113% Example 8 ExampleCompound 38 108% Example 9 Example Compound 73 119% Example 10 ExampleCompound 103 113% Example 11 Example Compound 104 121% Example 12Example Compound 122 113% Comparative Comparative Compound c1  80%Example 7 Comparative Comparative Compound c2  95% Example 8 ComparativeComparative Compound c3 100% Example 9 Comparative Comparative Compoundc4  94% Example 10 Comparative Comparative Compound c5  60% Example 11Comparative Comparative Compound c6  63% Example 12 ComparativeComparative Compound c7  95% Example 13 Comparative Comparative Compoundc8 101% Example 14 Comparative Comparative Compound c9  99% Example 15

Referring to the results of Table 2, it may be found that emissionefficiency was improved for Examples 4 to 12 when compared to that ofComparative Examples 7 to 15. From the results in Table 2, it may befound that organic electroluminescence devices including the compoundsaccording to example embodiments may attain high emission efficiency.

In Examples 4 to 12, a monoamine compound including a phenyl group as anadjacent group to a position where a phenanthryl group and an arylenelinker are connected is included. Without being bound by theory, it isbelieved that a volume near a phenanthryl group in which a LUMO orbitalwhich is related to electron transportation is distributed, isincreased, while maintaining amine properties, and the transportation ofelectrons from an emission layer to a hole transport layer becomesdifficult, and thus, the concentration of excitons in the emission layeris increased to increase the emission efficiency.

In Comparative Examples 9, 13, and 14, a compound in which a phenanthrylgroup and an amine group are connected via an arylene linker isincluded, but the phenanthryl group in the compounds included inComparative Examples 9, 13, and 14 is not substituted with a phenylgroup. Accordingly, without being bound by theory, it is believed thatblocking effect of electrons transported from an emission layer to ahole transport layer is not attained, and emission efficiency is lowerthan that of the examples.

In Comparative Examples 10 and 15, a compound in which a phenyl group issubstituted at a phenanthryl group is included, but the phenyl group isnot substituted at an adjacent position to a position where thephenanthryl group and an arylene linker are connected, that is, not atthe carbon of position 10 of the phenanthryl group, but at the carbon ofposition 3. Accordingly, without being bound by theory, it is believedthat the volume increase at an active position, where a LUMO orbitalwhich is related to electron transportation is distributed, is notattained, and emission efficiency is reduced when compared to that ofthe examples.

In Comparative Examples 11 and 12, the devices included a diaminecompound having a low HOMO energy level, such that hole injection from ahole injection layer to a hole transport layer may be deteriorated.Accordingly, emission efficiency was lower when compared to that of theexamples.

By way of summation and review, an organic electroluminescence devicemay be, for example, an organic device having a first electrode, a holetransport layer disposed on the first electrode, an emission layerdisposed on the hole transport layer, an electron transport layerdisposed on the emission layer, and a second electrode disposed on theelectron transport layer. Holes are injected from the first electrode,and the injected holes move via the hole transport layer and injectedinto the emission layer. Meanwhile, electrons are injected from thesecond electrode, and the injected electrons move via the electrontransport layer and injected into the emission layer. By recombining theinjected holes and electrons into the emission layer, excitons aregenerated in the emission layer. An organic electroluminescence deviceemits light using light emitted during the transition of the excitonsback to a ground state. The configuration of an organicelectroluminescence device is not limited thereto, and variousmodifications may be possible.

As described above, a monoamine compound according to an exampleembodiment may be used as a material for an organic electroluminescencedevice. The organic electroluminescence device including the monoaminecompound according to an example embodiment may attain high emissionefficiency. The present disclosure provides a monoamine compound used inan organic electroluminescence device having high emission efficiency.The present disclosure also provides an organic electroluminescencedevice having high emission efficiency

Example embodiments have been disclosed herein, and although specificterms are employed, they are used and are to be interpreted in a genericand descriptive sense only and not for purpose of limitation. In someinstances, as would be apparent to one of ordinary skill in the art asof the filing of the present application, features, characteristics,and/or elements described in connection with a particular embodiment maybe used singly or in combination with features, characteristics, and/orelements described in connection with other embodiments unless otherwisespecifically indicated. Accordingly, it will be understood by those ofskill in the art that various changes in form and details may be madewithout departing from the spirit and scope of the present invention asset forth in the following claims.

What is claimed is:
 1. A monoamine compound comprising: a centralnitrogen atom; a phenanthrene group bonded to the central nitrogen atomat 9th or 10th carbon position through a linker; and two functionalgroups bonded to the central nitrogen atoms, wherein one of the 9th and10th carbon positions is substituted with a substituted or unsubstitutedaryl group having 6 to 30 ring carbon atoms or a substituted orunsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and theother of the 9th and 10th carbon positions is bonded to nitrogen throughthe linker, the two functional groups are each independently asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms or asubstituted or unsubstituted heteroaryl group having 2 to 30 carbonatoms, the linker is a substituted or unsubstituted arylene group having6 to 30 ring carbon atoms or a substituted or unsubstitutedheteroarylene group having 2 to 30 ring carbon atoms, and whensubstituted, the substituent is at least any one of deuterium, halogenatom, cyano group, alkyl group, aryl group, arylsilyl group, substitutedor unsubstituted dibenzofuranyl group, substituted or unsubstituteddibenzothiophenyl group, substituted or unsubstitutedbenzonaphthothiophenyl group, and a substituted or unsubstitutedbenzonaphthofuranyl group.
 2. The monoamine compound as claimed in claim1, wherein the two functional groups are a substituted or unsubstitutedaryl group having 6 to 14 carbon atoms, or a substituted orunsubstituted heteroaryl group having 2 to 12 carbon atoms.
 3. Themonoamine compound as claimed in claim 1, wherein the two functionalgroups are a substituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted fluorenylgroup, a substituted or unsubstituted anthracenyl group, a substitutedor unsubstituted phenanthryl group, a substituted or unsubstitutedbiphenyl group, a substituted or unsubstituted terphenyl group, asubstituted or unsubstituted quarterphenyl group, a substituted orunsubstituted quinkphenyl group, a substituted or unsubstitutedsexyphenyl group, a substituted or unsubstituted triphenylene group, asubstituted or unsubstituted pyrenyl group, a substituted orunsubstituted benzofluoranthenyl group, a substituted or unsubstitutedchrysenyl group, a substituted or unsubstituted aryl group having 6 to30 carbon atoms, and a substituted or unsubstituted thiophenyl group,substituted or unsubstituted furanyl group, a substituted orunsubstituted pyrrolyl group, a substituted or unsubstituted imidazolylgroup, a substituted or unsubstituted thiazolyl group, a substituted orunsubstituted oxazolyl group, a substituted or unsubstituted oxadiazolylgroup, a substituted or unsubstituted triazolyl group, a substituted orunsubstituted pyridyl group, a substituted or unsubstituted bipyridylgroup, a substituted or unsubstituted pyrimidyl group, a substituted orunsubstituted triazinyl group, a substituted or unsubstituted triazolylgroup, a substituted or unsubstituted acridyl group, a substituted orunsubstituted pyridazinyl group, a substituted or unsubstitutedpyrazinyl group, a substituted or unsubstituted quinolinyl group, asubstituted or unsubstituted quinazolinyl group, a substituted or anunsubstituted quinoxalinyl group, a substituted or unsubstitutedphenoxazyl group, a substituted or unsubstituted phthalazinyl group, asubstituted or unsubstituted pyrido pyrimidinyl group, a substituted orunsubstituted pyridopyrazinyl group, a substituted or unsubstitutedpyrazino pyrazinyl group, a substituted or unsubstituted isoquinolinylgroup, a substituted or unsubstituted indolyl group, a substituted orunsubstituted benzoxazolyl group, a substituted or unsubstitutedbenzoimidazolyl group, a substituted or unsubstituted benzothiazolylgroup, a substituted or unsubstituted benzothiophenyl group, asubstituted or unsubstituted dibenzothiophenyl group, a substituted orunsubstituted thienothiophenyl group, a substituted or unsubstitutedbenzofuranyl group, a substituted or unsubstituted phenanthrolinylgroup, a substituted or unsubstituted thiazolyl group, a substituted orunsubstituted isoxazolyl group, a substituted or unsubstitutedoxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, asubstituted or unsubstituted benzothiazolyl group, a substituted orunsubstituted phenothiazinyl group, a substituted or unsubstituteddibenzosilolyl group, a substituted or unsubstituted dibenzofuranylgroup, a substituted or unsubstituted benzonaphthothiophenyl group, or asubstituted or unsubstituted benzonaphthofuranyl group.
 4. The monoaminecompound as claimed in claim 1, wherein one of the 9th and 10th carbonpositions is substituted with a substituted or unsubstituted aryl grouphaving 6 to 3014 ring carbon atoms or a substituted or unsubstitutedheteroaryl group having 2 to 12 ring carbon atoms.
 5. The monoaminecompound as claimed in claim 1, wherein one of the 9th and 10th carbonpositions is a substituted or unsubstituted phenyl group, a substitutedor unsubstituted naphthyl group, a substituted or unsubstitutedfluorenyl group, a substituted or unsubstituted anthracenyl group, asubstituted or unsubstituted phenanthryl group, a substituted orunsubstituted biphenyl group, a substituted or unsubstituted terphenylgroup, a substituted or unsubstituted quarterphenyl group, a substitutedor unsubstituted quinkphenyl group, a substituted or unsubstitutedsexyphenyl group, a substituted or unsubstituted triphenylene group, asubstituted or unsubstituted pyrenyl group, a substituted or anunsubstituted benzofluoranthenyl group, a substituted or unsubstitutedchrysenyl group, a substituted or unsubstituted thiophenyl group, asubstituted or unsubstituted furanyl group, a substituted orunsubstituted pyrrolyl group, a substituted or unsubstituted imidazolylgroup, a substituted or unsubstituted thiazolyl group, a substituted orunsubstituted oxazolyl group, a substituted or unsubstituted oxadiazolylgroup, a substituted or unsubstituted triazolyl group, a substituted orunsubstituted pyridyl group, a substituted or unsubstituted bipyridylgroup, a substituted or unsubstituted pyrimidyl group, a substituted orunsubstituted triazinyl group, a substituted or unsubstituted triazolylgroup, a substituted or unsubstituted acridyl group, a substituted orunsubstituted pyridagenyl group, a substituted or unsubstitutedpyrazinyl group, a substituted or unsubstituted quinolinyl group, asubstituted or unsubstituted quinazolinyl group, a substituted orunsubstituted quinoxalinyl group, a substituted or unsubstitutedphenoxazyl group, a substituted or unsubstituted phthalazinyl group, asubstituted or unsubstituted pyrido pyrimidinyl group, substituted orunsubstituted pyridopyrazinyl group, substituted or unsubstitutedpyrazino pyrazinyl group, substituted or unsubstituted isoquinolinylgroup, a substituted or unsubstituted indolyl group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstitutedN-arylcarbazolyl group, a substituted or unsubstitutedN-heteroarylcarbazolyl group, a substituted or unsubstitutedN-alkylcarbazolyl group, a substituted or unsubstituted benzoxazolylgroup, substituted or unsubstituted benzoimidazolyl group, a substitutedor unsubstituted benzothiazolyl group, substituted or unsubstitutedbenzocarbazolyl group, a substituted or unsubstituted Benzothiophenylgroup, a substituted or unsubstituted dibenzothiophenyl group, asubstituted or unsubstituted thienothiophenyl group, a substituted orunsubstituted benzofuranyl group, a substituted or unsubstitutedphenanthroline, a substituted or unsubstituted thiazolyl group, asubstituted or unsubstituted isoxazolyl group, a substituted orunsubstituted oxadiazolyl group, a substituted or unsubstitutedthiadiazolyl group, A substituted or unsubstituted benzothiazolyl group,a substituted or unsubstituted phenothiazinyl group, a substituted orunsubstituted dibenzosilolyl group, or a substituted or unsubstituteddibenzofuranyl group.
 6. The monoamine compound as claimed in claim 1,wherein the linker is a substituted or unsubstituted arylene grouphaving 6 to 14 ring carbon atoms or a substituted or unsubstitutedheteroarylene group having 2 to 12 ring carbon atoms
 7. The monoaminecompound as claimed in claim 1, wherein the linker is a substituted orunsubstituted phenyl group, a substituted or unsubstituted naphthylgroup, a substituted or unsubstituted fluorenyl group, a substituted orunsubstituted anthracenyl group, a substituted or unsubstitutedphenanthryl group, a substituted or unsubstituted biphenyl group, asubstituted or unsubstituted terphenyl group, a substituted orunsubstituted quarterphenyl group, a substituted or unsubstitutedquinkphenyl group, a substituted or unsubstituted sexyphenyl group, asubstituted or unsubstituted triphenylene group, a substituted orunsubstituted pyrenyl group, a substituted or an unsubstitutedbenzofluoranthenyl group, a substituted or unsubstituted chrysenylgroup, a substituted or unsubstituted thiophenyl group, a substituted orunsubstituted furanyl group, a substituted or unsubstituted pyrrolylgroup, a substituted or unsubstituted imidazolyl group, a substituted orunsubstituted thiazolyl group, a substituted or unsubstituted oxazolylgroup, a substituted or unsubstituted oxadiazolyl group, a substitutedor unsubstituted triazolyl group, a substituted or unsubstituted pyridylgroup, a substituted or unsubstituted bipyridyl group, a substituted orunsubstituted pyrimidyl group, a substituted or unsubstituted triazinylgroup, a substituted or unsubstituted triazolyl group, a substituted orunsubstituted acridyl group, a substituted or unsubstituted pyridagenylgroup, a substituted or unsubstituted pyrazinyl group, a substituted orunsubstituted quinolinyl group, a substituted or unsubstitutedquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, asubstituted or unsubstituted phenoxazyl group, a substituted orunsubstituted phthalazinyl group, a substituted or unsubstituted pyridopyrimidinyl group, substituted or unsubstituted pyridopyrazinyl group,substituted or unsubstituted pyrazino pyrazinyl group, substituted orunsubstituted isoquinolinyl group, a substituted or unsubstitutedindolyl group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted N-arylcarbazolyl group, a substituted orunsubstituted N-heteroarylcarbazolyl group, a substituted orunsubstituted N-alkylcarbazolyl group, a substituted or unsubstitutedbenzoxazolyl group, substituted or unsubstituted benzoimidazolyl group,a substituted or unsubstituted benzothiazolyl group, substituted orunsubstituted benzocarbazolyl group, a substituted or unsubstitutedBenzothiophenyl group, a substituted or unsubstituted dibenzothiophenylgroup, a substituted or unsubstituted thienothiophenyl group, asubstituted or unsubstituted benzofuranyl group, a substituted orunsubstituted phenanthroline, a substituted or unsubstituted thiazolylgroup, a substituted or unsubstituted isoxazolyl group, a substituted orunsubstituted oxadiazolyl group, a substituted or unsubstitutedthiadiazolyl group, A substituted or unsubstituted benzothiazolyl group,a substituted or unsubstituted phenothiazinyl group, a substituted orunsubstituted dibenzosilolyl group, or a substituted or unsubstituteddibenzofuranyl group
 8. An organic electroluminescence device,comprising: a first electrode; a hole transport region disposed on thefirst electrode; an emission layer disposed on the hole transportregion; an electron transport region disposed on the emission layer; anda second electrode disposed on the electron transport region, wherein atleast one of the hole transport region, the emission region, and theelectron transport region includes a monoamine compound, wherein themonoamine compound comprising: a central nitrogen atom; a phenanthrenegroup bonded to the central nitrogen atom at 9th or 10th carbon positionthrough a linker; and two functional groups bonded to the centralnitrogen atoms, wherein one of the 9th and 10th carbon positions issubstituted with a substituted or unsubstituted aryl group having 6 to30 ring carbon atoms or a substituted or unsubstituted heteroaryl grouphaving 2 to 30 ring carbon atoms, and the other of the 9th and 10thcarbon positions is bonded to nitrogen through the linker, the twofunctional groups are each independently a substituted or unsubstitutedaryl group having 6 to 30 carbon atoms or a substituted or unsubstitutedheteroaryl group having 2 to 30 carbon atoms, the linker is asubstituted or unsubstituted arylene group having 6 to 30 ring carbonatoms, and when substituted, the substituent is at least any one ofdeuterium, halogen atom, cyano group, alkyl group, aryl group, arylsilylgroup, substituted or unsubstituted dibenzofuranyl group, substituted orunsubstituted dibenzothiophenyl group, substituted or unsubstitutedbenzonaphthothiophenyl group, and a substituted or unsubstitutedbenzonaphthofuranyl group.
 9. The organic electroluminescence device asclaimed in claim 8, wherein the hole transport region includes themonoamine compound.
 10. The organic electroluminescence device asclaimed in claim 9, wherein the hole transport region includes: a holeinjection layer disposed on the first electrode; and a hole transportlayer disposed on the hole injection layer, and wherein the holetransport layer includes the monoamine compound.
 11. The organicelectroluminescence device as claimed in claim 10, wherein the holetransport layer makes contact with the emission layer.
 12. The organicelectroluminescence device as claimed in claim 9, wherein the holetransport region includes: a hole injection layer disposed on the firstelectrode; a first hole transport layer disposed on the hole injectionlayer; and a second hole transport layer disposed on the first holetransport layer, the second hole transport layer being adjacent to theemission layer, wherein the second hole transport layer includes themonoamine compound.